Azo dyes.



HEINRICH JORDAN arm WILHELM NEELMEIEE,

or tn'vnaxusnn, unenconcerts,

4 GERMANY, ASSIGNORS TO SYNTHETIC PATENTS 00., INQ, OF NEW Y'DRK, N. Y.,A

CORPORATION 01F NEW YORK.

nzoeras.

No Drawing.

.710 (ZZZ whom it may concern:

Be it known that we, Hnmnioii JORDAN and TILHELM NEELMEER, doctorso'fnh1l- I osophy, chemists, citizens'of the Gefman Empire, residing atLeverkusen, near co-- L logne-on-the-Rhine, Germany, have inventc z fa ce s 6 2 ed new and useful Improvements in New Azo Dyes, of which thefollowing is a specification.

Vie have found that new and valuable azodyestuffs can be obtained bycon1hin= ing the diazo compounds prepared from diand tri-azolederivatives of oxyarylcarhoxylic acid compounds havingmost probably thefollowing general formula;

on (1-) R coon 2 \-NH2 I X R stands for an aryl radical, c. C l-1 H Xstanding for -N=, or a carbon linked together with -H, CH -C5H or thelike, such as aminoniethylbenzimidazolepara-salicylic acidaminobenziznidazole ortho salicylic acid,aminobenzimidazole-para-sulfoor chlorosalicylic acid,para-aminophenyl-l-aziminosalicylic acid cemcoon a N -N H:

ISSN/ and the respective derivatives of 'cresotinic acid, etc, with azo.dyestufli components e. g.

naphthol sulfo'nic acids, aminonaphthol sul- When printed with acetateof chromium on the' fibe r a, pure blue-red-shade is oh Specification 0Letters iatent Application filed Au gust 2:8,

Patented Feb, 2, 1%15; 1913. Serial'No. ?87,l38.

salts dark powders soluble in water generally with a yellow to red tocoloration and in concentrated sulfuric acid witli' a red to ebluish-redcoloration and" yielding' upon reduction with acetic acid andjzmc powdera compound of the above given general formula:-

i 0811; coon yam are'diazotized with 69 parts of sodium nitrite in 200parts of water at 2025 C. and 270 parts of hydrochloric acid 19 B. Thediazo' compound thus obtained is then Stirred into a cold solution of465 part-s of the 'disodium salt of acetyl-]..8-amino- 1naphthol-.6-disulfonic acid containing 250 parts of soda. Afterstirring'tlie' combination is soon complete and the dye'stufl is saltedout and filtered off. It is after being dried and pulverized in theshape of its sodium salt a brown-red powder soluble in. water with ablue red coloration and in concentrated sulfuricacid with a red-bluecoloration;- and yielding upon reduction with zincpowdeiand acetic acidaminobenzimidazole-ortho-aniinosalic lic acid andl-acetylamino-7-ainino-S-naplit 10l-'-l.6-dl5lllionic acid. It has in afree state most probably the formula:

on NH-COCH tained fast to chlor-in and to soap, It dyes also chromewool,

bluish md Other azo dyestufi components may be used,lacetylamino-S-naphthol-ddd1-- snlfonic acid, naphthol-sulfonic acids,1-'mc-- noethyloxy-8-naphthol-3.6disclfonic acid.

In referring to the products of the present invention asazoles orpolyaaoles, etc, these terms a) tended to-include both the ilni-fdazoles vzoleslin' which the X of the above formula stands or --N: andthe 'as'imino derivatives ,(triazolesl in which the X stands for asubstituted carbonatom.

We claim 1. The new azo dyestuffs, having as one component thereof anazole derivative of an .oxy' 'carboxylic acid, which are after beingdried and pulverized. in the shape of their alkaline salts dark owderssoluble in water generally with a ye low to red to bluish-red colorationand in concentrated sulfuric acid with a red to blue-red coloration;yielding upon reduction with acetic acid and zinc powder an'oxya'ryl-carboxylic acid compound containing a heterocyclic nuclens andan axn'in; and furnishing on the fiber from yellow to red to violetchrome lakes'fast to bhlorin and to soap, substantially as described I y2- The'new azo dyestuffs, having as one component thereof an imidazolederivative of an oxycarboxyiic'acid,which are after he I ing dried andpulverized in the shape of their alkaline salts dark powders soluble inwater generally with'a yellow to red to bl u ish-red' coloration and inconcentrated" sill-- furie acid with a red to blue red' coloration;yielding upon reduction with acetic acid and zinc powder anoxyarylcarboxylic acid compound containing a heterocyclic nucleus and'ajnamin; and furnishing'on the fiber from yellow-- to red toyiole'tchrome lakes fast to chlorinv and to 'soap, substantially asdescribed.

3, ;The new azo dyestuffs having as com-- ponents an azole derivative ofan oxycarb ylic acid and a naphthalene sulfonic acid, which-are afterbeing dried and pulverized in the shape. of their alkaline salts darl;powders soluble in water generally with yellow to red to bluish-redcoloration c, in concentrated. sulfuric acid with a red t blue-redcoloration, yielding upon reduction,

with acetic. acid and zinc powder an oxyin the shape of its sodium salta brown .n-

nowder soluble, in water w th a redeblnc rr: .uctims with zinc powderand acetic acid 110 nnpoi m d containin g a nd an. :iinin; and furrm tored "iori' qi and to a red to' blue-red coloration; yielding uponrednctionwith acetic acid and zinc powder an oxyarylcarboxylic acidcompound con taining a'heterocyclic nucleus and an ending andfurnishing. on the fiber from-yellow to red to violet chrome lakes fastto chlorin and to soap, substantially as described.

5. Thenew azo d'yestuifs having as com- PQHBDES an az'ole derivative ofan oxycar boxylidacid and a naphthol sulfonic acid which are after beingdried and pulverized in the shape oftheir alkaline salts dark powderssoluble in water gen'erally-withyeL low to red. to bluish-red colorationand in concentrated sulfuric acid with a red to blue red coloration;yielding upon reduction with acetic acid and Zinc powderanox'yarylcarboxylic acid compound containing a hetero cyclic nucleus andan amin; and furnishing on the fiber from yellowto red to violet chromelakes fast to chlorin and ,to soap,

snbstanti ally as described.

6. The new 'aZo dyestufls having as com ponents an imidazole derivativeof an oxycarboxylic acid and a naphthol snlfonic acid, which are afterbeing dried and pulverized in the shape of their alkaline salts darkpowders soluble in water generally with a yellow to to bluish-redcoloration and in conce'nr" ated sulfuric aCld"\V1th fl red to blue-red.nloration yielding upon reduction tic acid and zinc powder an oxyarylla d ccnipxnlndcontaining a hetc icleus' and ennin and furnishing on. theliber fom yellow to red to vviolet chrome lakes'fa to chlorin and tosoap, substantially as described.

7. The new azo dyestuffs having in a free state most probably thetor-mule:

coloration and in concentrated sulrurlc acid w a red-blue coloration;ylelding upon aminabenzimidazole orhoamixms soap, subsizmtmlly asdessz'mwi "i 0111" hands in the presence of two ,sub-

acid. and l-acetyiamino-Y-aunin0-8 hscribing Witnesses.

5ha lene4l3-dis'nlfonic acid; :umfl. i J "Lien RICH JORDAN.

printed on the fiber with acetata 0?: Qhrw VVILHELM NEELMEFQQ.

min bi e-red shades fast to chlorin and to Witnesses:

' JULIUS FESTNER,

ALBERT NE'FEH.

In te'stinmzly whereof was Eur-Jehereuntu

